As usual on Literotica, these kinds of stories are a lot more fun if you read the chapters in sequence. But of course you don't have to. Enjoy!
* * *
"Regular tutoring" was, at first, something I insisted we set up at school. Natalie was resistant at first; she'd pouted, her skirted legs indignantly crossed, as we spoke about it before school a couple days after she'd babysat. "I don't get it," she said slowly. "Your ugly wife has basically given us a free pass to fuck in her bed. Why wouldn't we take advantage of her stupidity?"
"You don't get it, Natalie," I explained again, carefully. "I can't just ask her to leave the house every time you come over for 'tutoring.' She's not as dumb as you think; she'd figure it out soon. Besides, where would you suggest I tell her to go?"
She glared at me for a long second. "See, this is the problem with you," she said calmly. "You're too much of a pussy to stand up to your woman. I've obviously seen it myself a few times now, but apparently it's a universal thing with you." She shrugged. "Fine. It's one thing to let a woman like me control your cock, but if you're going to let a pitiful fat bitch like your wife control your brain, well, I guess I'll just have to wait you out. Too bad; I thought that maneuver the other night with the milk showed me something I could use, something I could respect about you. But I guess not."
She stood up, smoothing her skirt, looking very prim for today's classes. As always, she was expertly made up, her taste excellent. I couldn't help picturing her naked as she stood there. "We'll meet here, after school or whenever else I feel like it. You can pleasure me however I like, and I'll blow you. It won't be the same as what I got in your bed the other night, but I guess I'll just have to put up with your lack of imagination until you decide to grow a pair. Not literally; I know you've already got testes." She eyed me up and down. "We can start this afternoon, on my free period."
And she'd shown up on schedule, locking the door, folding her clothing, and attacking me with her usual soullessness; we'd ended up 69ing on the desk. Naturally, I'd been on the bottom. At one point I'd thought dully about how surreal all this was, as I watched her narrow, naked ass writhing above me, her skinny thighs clamped hard against my ears as I lapped desperately at her trimmed pussy. She tasted coppery and warm, the flesh around her opening turning bright pink as I did my best. My chin was plastered against her smooth thighs.
"Uh," she'd grunted softly, the fingers of both her hands clutching my balls. "Suck on that pussy, Mr Herrick. Keep going." She'd been doing some very good work of her own, giving her clinical and precise effort as she ran her mouth rhythmically up and down my straining cock. Due to the reverse angle, she couldn't give my balls her usual attention, but my pubes were now completely plastered down by her thick saliva.
This was my very first 69, and I too was symied by the reverse angle. My wife had always been embarrassed about getting her pussy munched, so my practice in that area was badly outdated. But I knew Natalie wasn't very experienced either, so I hoped my enthusiasm could make up for whatever technique I lacked. I was, of course, aware that ladies liked having their clit played with during oral, but Natalie was so tight it was hard to find hers. So I pointed my tongue, poked it as far underneath her as I could get, and buried my nose in her crotch as I stabbed vaguely at where her hair began.
She tolerated me for a few more minutes, continuing to lavish her attention on my dick, but it was clear already that she was in no danger of cumming, and once she realized that, she figured she'd just go ahead and end things quickly. She shifted her position, driving her ass into the air as she pulled herself away from my tired lips and tongue, then doubled down on my cock, arching her back to straighten her neck so that she could take me deep; as I looked down past my own hairy torso, I caught her bulging throat and the underside of her dangling little breasts, the nipples as hard as usual, one hand still working my balls on the far side; the other hand was directly above my head, prying herself open from below so that she could frig herself. All I could smell was her.
I saw a trickle of saliva inch slowly down my shaft, and her lips followed; her chin was brushing my matted pubes now, her throat choking my glans as she gagged, and it was all too much; as usual, she took my cum like a pro, not needing my strangled warning, her fingers' sure grip on my balls telling her what was going to happen. Her swollen throat bobbed and quivered as I fired my semen into it, gasping and moaning. The long-fingered hand on her pussy didn't stop above me; this woman knew her own anatomy, and those fingers did precisely what they needed to do. I watched, enthralled, as her thumb and forefinger found her elusive clit, the middle finger digging grimly for her g-spot, and then she was twitching, her mouth finished with my slimy penis, gasping as she came.
She laid her head on the desk between my legs, her mouth opening in orgasm, her nose brushing my sweaty balls. The pussy above me shone with her fluids, now frothing slightly as she stirred herself gently down; a thin trail of clear fluid ran faintly down her thigh, and I vainly tried to lick at it. Her head snapped back up to look at me, though, and I could have sworn she appreciated the effort. At least a little bit.
"I was less excited by that than you were," she told me coolly after it was over. "Figure out a way to get me into bed," she advised gravely. "Soon. I need sex."
"I'll do my best."
"Quickly, or I might have to find some other willing male." She touched up her pale pink lipstick, then patted my shoulder. "Thanks for the tutoring. I'll see you tomorrow morning for Student Council."
* * *
The main agenda item the next morning was the annual car wash, and there was dissention in the ranks from the start. "Absolutely not," I told the assembled kids. "There was trouble last year."
"Trouble?" Natalie said sharply, her position as president giving her the right to snap at me. "No way. What kind of trouble?"
"Well, there were complaints. You know, about the swimsuits."
"They're bikinis, Mr Herrick," she told me flatly. "Nobody actually swims in them."
"Be that as it may." I frowned and tried to be assertive. "Some of the customers last year told Mr McCarron they didn't think it was appropriate for our students to be washing cars in their... swimsuits. They complained about the boys, too," I lied defensively.
"This is crap!" It was Natalie's friend Chloe, and I shuddered as I thought about her nipples hardening while she saw footage of me getting a blowjob. "This is always our biggest fundraiser, Mr Herrick, and you know the reason why." She blinked and arched her back, leaving me in no doubt that she was right; hell, even I'd have paid to let Chloe wash my car just to see her wet boobs.